[EN] METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE<br/>[FR] PROCÉDÉ DE PRÉPARATION DU 2'-O-FUCOSYLLACTOSE
申请人:BASF SE
公开号:WO2017153452A1
公开(公告)日:2017-09-14
The present invention relates to a method for preparing 2'-O-fucosyllactose and to the protected fucosyl donor of the formula (I) used in this method. The method comprises reacting the fucose derivative of the formula (I) below with the compound of the general formula (II), in the presence of an activating reagent. In the formulae (I) and (II), the variables are each defined as follows: X is Br or a S-bound radical, namely -SCN, -S(O)n-RX1 or -S-RX2, wherein RX1 preferably is an optionally substituted phenyl, and RX2 preferably is C1-C4-alkyl, 2-oxazolin-2-yl, 2-thiazolin-2-yl, benzoxazol-2-yl, benzothiazol-2-yl or pyridin-2-yl; RSi are the same or different and are radicals of the formula SiRaRbRc, wherein Ra, Rb and Rc preferably are each methyl; R1 is a C(=O)-R11 radical or an SiR12R13R14 radical, wherein R11 is preferably methyl, phenyl or tert-butyl, and R12, R13 and R14 preferably are each methyl; R2 are the same or different and are C1-C8-alkyl or together form a linear C3-C6-alkanediyl, which is unsubstituted or has 1 to 6 methyl groups as substituents; R3 are the same or different and are C1-C8-alkyl or together form a linear C1-C4-alkanediyl, which is unsubstituted or has 1 to 6 methyl groups as substituents.
本发明涉及一种制备2'-O-岩藻糖乳酸的方法,以及在该方法中使用的公式(I)的保护岩藻糖供体。该方法包括在活化试剂存在下,将下式(I)的岩藻糖衍生物与通用式(II)的化合物反应。在公式(I)和(II)中,变量的定义如下:X为Br或S-结合基团,即-SCN,-S(O)n-RX1或-S-RX2,其中RX1优选为可选取代的苯基,RX2优选为C1-C4-烷基,2-噁唑烷-2-基,2-噻唑烷-2-基,苯并噁唑烷-2-基,苯并噻唑烷-2-基或吡啶-2-基;RSi相同或不同,且为公式SiRaRbRc的基团,其中Ra,Rb和Rc优选为甲基;R1为C(=O)-R11基团或SiR12R13R14基团,其中R11优选为甲基,苯基或叔丁基,R12,R13和R14优选为甲基;R2相同或不同,为C1-C8烷基,或共同形成线性C3-C6烷二基,其未取代或有1至6个甲基取代基;R3相同或不同,为C1-C8烷基,或共同形成线性C1-C4烷二基,其未取代或有1至6个甲基取代基。